Skip to Main content Skip to Navigation
Journal articles

Synthesis and conformational behavior of pseudopeptides containing delta-azaproline. A cis conformational preference for Xaa(1)-delta-azaPro bond

Abstract : delta-Azaproline, a new bis-nitrogen proline surrogate has been used in order to control the conformation of an AA-Psi Pro bond. Conformational analysis of Xaa(1)-delta-azaPro-Xaa(3) performed by NMR, IR experiments, and molecular modeling revealed a preference for a trans conformation of the Xaa(1)-delta-azaPro bond when delta-azaPro is protected by a Boc group. The removal of the Boc protection leads to the establishment of a C-10 pseudocycle via a hydrogen bond network favoring the cis conformation of the Xaa(1)-delta-azaPro bond.
Document type :
Journal articles
Complete list of metadata

https://hal.univ-lorraine.fr/hal-01498198
Contributor : Lcpm Ul <>
Submitted on : Wednesday, March 29, 2017 - 4:52:15 PM
Last modification on : Tuesday, March 30, 2021 - 3:24:38 AM

Identifiers

Collections

Citation

Emelyne Humbert-Voss, Axelle Arrault, Brigitte Jamart-Grégoire. Synthesis and conformational behavior of pseudopeptides containing delta-azaproline. A cis conformational preference for Xaa(1)-delta-azaPro bond. Tetrahedron, Elsevier, 2014, 70 (2), pp.363-370. ⟨10.1016/j.tet.2013.11.049⟩. ⟨hal-01498198⟩

Share

Metrics

Record views

152